EP2765129B1 - Phenylisoxazolinverbindung mit herbiziden eigenschaften und ihre verwendung - Google Patents

Phenylisoxazolinverbindung mit herbiziden eigenschaften und ihre verwendung Download PDF

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EP2765129B1
EP2765129B1 EP12838839.4A EP12838839A EP2765129B1 EP 2765129 B1 EP2765129 B1 EP 2765129B1 EP 12838839 A EP12838839 A EP 12838839A EP 2765129 B1 EP2765129 B1 EP 2765129B1
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methyl
group
formula
racemate
enantiomer
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EP2765129A4 (de
EP2765129A1 (de
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Young Kwan Ko
Gyu Hwan Yon
Jae Wook Ryu
Dong Wan Koo
Jun Ho Nam
Sung Wan Pyo
Jae Min Hwang
Suk Jin Koo
Ki Hwan Hwang
Dong Guk Lee
Man Seok Jeon
Nam Gyu Cho
Sung Hun Kim
Jong Su Lim
Kun Hoe Chung
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Moghu Research Center Ltd
Korea Research Institute of Chemical Technology KRICT
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Moghu Research Center Ltd
Korea Research Institute of Chemical Technology KRICT
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to a phenylisoxazoline-based compound having herbicidal activity and a use thereof, and in particular, to an ortho-substituted phenylisoxazoline-based compound with 2,6-difluorobenzyloxymethyl represented by Formula 1, a racemate or enantiomer thereof, a herbicide including the phenylisoxazoline-based compound, or the racemate or enantiomer thereof as an active ingredient, and a method of selectively controlling grass weed with the phenylisoxazoline-based compound, or the racemate or enantiomer thereof before or after the grass weed emerges.
  • 4,983,210 discloses an isoxazoline compound represented by Formula 2a below: wherein, R1 indicates a C1 to C12 alkyl group, a C3 to C7 cycloalkyl group, a substituted or unsubstituted phenyl group, or a saturated or unsaturated 5 to 6-membered heterocyclic group, R2, R3, R4, R5, and R6 each indicates a hydrogen atom, an alkyl group or a benzyl group, and R7 indicates a substituted or unsubstituted C2 to C6 alkenyl, C5 to C7 cycloalkenyl, phenyl, naphthyl, or thienyl.
  • R1 indicates a C1 to C12 alkyl group, a C3 to C7 cycloalkyl group, a substituted or unsubstituted phenyl group, or a saturated or unsaturated 5 to 6-membered heterocyclic group
  • US Patent No. 4,983,210 is the first from among inventions relating to the same kinds of compound, and Formula 2a represents any possible compounds thereof.
  • 128 compounds are disclosed with their structures.
  • the patent discloses in its example that at an application rate of 1 kg/ha before weeds emerged, rape showed tolerance, and another example discloses that sunflower had tolerance at an application rate of 0.5 kg/ha at which a herbicidal activity toward weeds was obtained.
  • the weeds were not specified.
  • US Patent No. 5,262,388 disclosed a herbicidal compound having nitrophenylisoxazoline represented by Formula 2b: wherein, X indicates a nitro group, Y indicates a hydrogen atom or a halogen group, and R indicates a C1 to C6 alkyl group.
  • the structure of Formula 2b is equivalent to the structure of Formula 2a disclosed in US Patent No. 4,983,210 in which R1 and R7 are each substituted with a phenyl group, and the structure of Formula 2b is included in the scope of the claims of the preceding patent but not in Examples thereof.
  • the structure of Formula 2b has high effects on barynardgrass (Echinochloa crusgalli ), which has not been disclosed in the preceding patents.
  • Japanese Publication Patent No. 1997-143171 discloses an isoxazoline compound represented by Formula 2c below: wherein, R1 indicates an alkyl group or an aryl group, X indicates an oxygen or an NOR4 group, R2 indicates an alkyl group, and R3 indicates a substituted aryl group.
  • Japanese Publication Patent No. 2001-158787 discloses a pyrazole isoxazoline compound represented by Formula 2d below: wherein, R1, R2, and R3 each indicates a hydrogen, a halogen group, a nitro group, a cyano group, a hydroxy group, a haloalkyl, or a substituted phenyl, R4, R5, R6, R7, and R8 each indicates a hydrogen, haloalkyl, haloalkenyl, or substituted phenyl, and R9 indicates a substituted aryl.
  • R1, R2, and R3 each indicates a hydrogen, a halogen group, a nitro group, a cyano group, a hydroxy group, a haloalkyl, or a substituted phenyl
  • R4, R5, R6, R7, and R8 each indicates a hydrogen, haloalkyl, haloalkenyl, or substituted phenyl
  • R9 indicates a substitute
  • US Patent No. 6,838,416 discloses a thiophene isoxazoline compound represented by Formula 2e below: wherein, X1, X2, and X3 each indicates a hydrogen atom, an alkyl group, a halogen group, a methoxy group, or a nitro group, and Y1, Y2, and Y3 each indicates a hydrogen atom or a fluorine atom.
  • the structures of Formulae 2d and 2e conform to the chemical structure of Formula 2a, but are not included in examples of Formula 2a, and the structures of Formulae 2d and 2e have stability with respect to rice and high effects on Echinochloa crusgalli , which is a major weed with respect to rice.
  • the compounds represented by Formulae 2a to 2e have not been used as commercially available chemicals for culturing crops. This is because an amount thereof required is as high as about 1 kg/ha and thus, compared to recently developed other kinds of chemicals, their economical efficiency is low. However, understanding structural activity relationships for the reduction in the use rate is very poor. Meanwhile, in agriculture, emergence of herbicide-resistant weeds is a big issue to be solved, and to control resistant weeds, new kinds of herbicides showing a novel action need to be developed. Isoxazoline-based herbicidal compounds are known to have a different herbicidal action.
  • isoxazoline herbicides are reported to inhibit biosynthesis of a plant cell wall, and their inhibitory manners differ from those of other cell-wall inhibiting agents (Lee JN et al., 2007. Mode of action of a new isoxazoline compound. Proc. 21st APWSS tConf. 597-601, Colombo, Sri Lanka). Accordingly, it is highly likely to develop a novel herbicide for controlling resistant weeds from isoxazoline-based herbicidal compounds. against this backdrop, inventors of the present invention studied structural activities relationships regarding each substituent of isoxazoline-based herbicidal compounds to develop novel materials with higher herbicidal effects than the materials disclosed in the preceding patents.
  • One or more embodiments of the present invention provide an ortho-substituted phenylisoxazoline-based compound with 2,6-difluorobenzyloxymethyl represented by Formula 1, or a racemate or enantiomer thereof.
  • One or more embodiments of the present invention provide a herbicide including the ortho-substituted phenylisoxazoline-based compound, or the racemate or enantiomer thereof as an active ingredient.
  • One or more embodiments of the present invention provide a method of selectively controlling grass weed comprising treating with the ortho-substituted phenylisoxazoline-based compound, or the racemate or enantiomer thereof before or after the grass weed emerges.
  • the phenylisoxazoline-based compound has 4 or more times as high as the herbicidal activity of typical isoxazoline-based compounds, and thus, its stability with respect to major crops, such as bean, corn, cotton, wheat, or rice, is high, and when used, major grass weeds, such as barnyardgrass (Echinochloa crusgalli ), blackgrass ( Alopecurus myosuroides), crabgrass ( Digitaria sanguinalis ), or annual bluegrass ( Poa annua ), are effectively controlled. Accordingly, when the phenylisoxazoline-based compound is used, productivity of crops may improve.
  • major grass weeds such as barnyardgrass (Echinochloa crusgalli ), blackgrass ( Alopecurus myosuroides), crabgrass ( Digitaria sanguinalis ), or annual bluegrass ( Poa annua ).
  • An aspect of the present invention provides an ortho-substituted phenylisoxazoline-based compound with 2,6-difluorobenzyloxymethyl represented by Formula 1, or a racemate or enantiomer thereof: wherein, R1 indicates a C1 to C4 alkyl group, a halogen group, or a haloalkyl group, R2 indicates a hydrogen, a methyl group, or an ethyl group, and R3 and R4 each indicates a fluorine.
  • R1 indicates a methyl group, a fluorine group, a chorine group, a bromine group, or a trifluoromethyl group
  • R2 indicates a hydrogen, a methyl group, or an ethyl group
  • R3 and R4 each indicates a fluorine.
  • the phenylisoxazoline-based compound, or the racemate or enantiomer is selected from
  • Another aspect of the present invention provides a herbicide including the phenylisoxazoline-based compound, or the racemate or enantiomer thereof as an active ingredient.
  • the herbicide may include the phenylisoxazoline-based compound, a racemate or enantiomer thereof as a single active ingredient in an amount of 0.5 to 80 wt% based on the final product, but the amount of the phenylisoxazoline-based compound, a racemate or enantiomer thereof is not limited thereto.
  • the herbicide may include the phenylisoxazoline-based compound, a racemate or enantiomer thereof, as an active ingredient of a mixed product, in an amount of 0.5 to 40 wt% based on the final product, but the amount of the phenylisoxazoline-based compound, a racemate or enantiomer thereof is not limited thereto.
  • the herbicide may include a carrier, a surfactant, a dispersant, or an adjuvant, which are commonly used in formulating agricultural pesticides.
  • the herbicide may be used in an aqueous formulation, an emulsifiable concentrate formulation, a powder formulation, a suspension formulation, or a liquid formulation, but the formulation for the herbicide is not limited thereto.
  • the herbicide may be directly used, or diluted in an appropriate medium before use.
  • a spray amount of the herbicide may be hundreds to thousands liters per hectare (ha), but is not limited thereto.
  • the herbicide may include a surfactant in an amount of about 0.1 to 20 wt%, or a solid or liquid diluent in an amount of 0 to 99.9 wt%, but the amounts of the surfactant and the diluent are not limited thereto.
  • the phenylisoxazoline-based compound, or the racemate or enantiomer thereof may be used alone, or together with a herbicidal compound, a safener, a synergistic agent, or a plant growth regulator.
  • the herbicidal compound may include at least one selected from an acetyl-CoA carboxylase (ACC) inhibitor, an acetolactate synthase (ALS) inhibitor, amide, auxinic herbicide, an auxin transport inhibitor, a carotenoid biosynthesis inhibitor, an enolpyruvylshikimate-3-phosphate synthase (ESPS) inhibitor, a glutamine synthetase inhibitor, a lipid biosynthesis inhibitor, a mitosis inhibitor, a protoporphyrinogen IX oxidase inhibitor, a photosynthesis inhibitor, a cell-wall biosynthesis inhibitor, and other herbicides.
  • ACC acetyl-CoA carboxylase
  • ALS acetolactate synthase
  • amide auxinic herbicide
  • auxin transport inhibitor a carotenoid biosynthesis inhibitor
  • an enolpyruvylshikimate-3-phosphate synthase (ESPS) inhibitor an enolpyruvyl
  • Another aspect of the present invention provides a method of preparing the isoxazoline-based compound represented by Formula 1 by a reaction of compounds represented by Formulae 3 and 4 or a reaction of compounds represented by Formulae 5 and 6: in Formulae 3 to 6, R1, R2, R3, and R4 are the same as explained in connection with Formula 1, and X indicates chlorine or bromine.
  • the compound represented by Formula 1 may be prepared according to Reaction Scheme 1 below. In detail, a hydroxy compound represented by Formula 3 is reacted with a compound represented by Formula 4 in a base condition to obtain the compound represented by Formula 1.
  • R1, R2, R3, and R4 are the same as explained in connection with Formula 1, and X indicates chlorine or bromine.
  • the base when NaOH or KOH is used as a base, the base may be excessively used with respect to the hydroxyl compound of Formula 3 in a mixed solvent of water and an organic solvent, and examples of the organic solvent used herein are toluene, dioxane, tetrahydrofuran, and 1,2-dichloroethane.
  • the reaction may be promoted by adding a phase-transition catalyst to the reaction mixture.
  • phase-transition catalyst examples include tetrabutylammonium bromide, tetramethylammonium bromide, tetraethylammonium bromide, tetrabutylammonium iodide, and tetrabutylammonium hydrogen sulfate.
  • the compound of Formula 4 may be used in an amount of 1 to 1.5 mol based on the hydroxy compound of Formula 3, and the reaction may be performed at a temperature of 50 to 100°C. When the reaction stops, the reaction solution is cooled, and a separated organic layer is washed with water, and then, dried and concentrated, followed by refining through column chromatography.
  • an available solvent herein may be anhydrous tetrahydrofuran anhydrous dimethylformamide, or anhydrous toluene.
  • an amount of the base may be, based on the hydroxy compound of Formula 3, in a range of 1.0 to 1.2 e.q., and an amount of the compound of Formula 4 may be in a range of 1.0 to 1.5 e.q..
  • the reaction temperature may be in a range of -50 to 30°C.
  • the hydroxy compound of Formula 3 may be prepared as illustrated in Reaction Scheme 2 below:
  • R1 and R2 are the same as explained in connection with Formula 1, and X indicates chlorine or bromine.
  • the oxime compound (Formula 7) is reacted with 1.0 to 1.2 e.q. of N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS) in an organic solvent, such as dichloromethane, dichloroethane, toluene, dioxane, or tetrahydrofuran at a temperature of -20 to 30°C to prepare a halo-oxime compound (Formula 5), and the obtained halo-oxime compound (Formula 5) is reacted with an unsaturated alcohol compound (Formula 8) in an amount of 1.0 to 1.3 e.q.
  • NBS N-bromosuccinimide
  • NCS N-chlorosuccinimide
  • the base may include an inorganic salt, such as NaHCO3, KHCO3, Na2CO3, or K2CO3, or an organic salt, such as a trialkylamine or a pyridine.
  • An amount of the base may be in a range of 1.0 to 1.5 e.q. based on the oxime compound (Formula 7).
  • phase-change catalyst may be further used, and examples of the phase-change catalyst are tetrabutyl ammoniumbromide, tetramethylammoniumbromide, tetraethylammoniumbromide, tetrabutylammonium iodide, and tetrabutylammonium hydrogensulfate, and an amount of the phase-change catalyst may be in a range of 0.01 to 0.1 e.q.
  • the reaction solution i added to an aqueous solution, and an organic layer obtained by extracting with an organic solvent is dried and concentrated and refined by column chromatography.
  • the compound represented by Formula 1 may be prepared according to Reaction Scheme 3 below:
  • the oxime compound (Formula 7) is reacted with 1.0 to 1.2 e.q. of N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS) in an organic solvent, such as dichloromethane, dichloroethane, toluene, dioxane, or tetrahydrofuran at a temperature of -20 to 30°C to prepare a halo-oxime compound (Formula 5), and the obtained halo-oxime compound (Formula 5) is reacted with an unsaturated compound (Formula 6) in an amount of 1.0 to 1.3 e.q.
  • NBS N-bromosuccinimide
  • NCS N-chlorosuccinimide
  • the base may include an inorganic salt, such as NaHCO3, KHCO3, Na2CO3, or K2CO3, or an organic salt, such as a trialkylamine or a pyridine.
  • An amount of the base may be in a range of 1.0 to 1.5 e.q. based on the oxime compound (Formula 7).
  • phase-change catalyst may be further used, and examples of the phase-change catalyst are tetrabutyl ammoniumbromide, tetramethylammoniumbromide, tetraethylammoniumbromide, tetrabutylammonium iodide, and tetrabutylammonium hydrogensulfate, and an amount of the phase-change catalyst may be in a range of 0.01 to 0.1 e.q.
  • the reaction solution is added to an aqueous solution, and an organic layer obtained by extracting with an organic solvent is dried and concentrated and refined by column chromatography.
  • reaction mixture was stirred at room temperature overnight, and then washed with water, and then, an separated organic layer was dried and concentrated by using magnesium sulfate, and then, purified by column chromatography to obtain 70 g of (5-methyl-3-o-tolyl-4,5-dihydroisoxazole-5-yl)methanol.
  • the obtained compound was dissolved in 1 L of toluene, and then, 1 L of water, 90 g of NaOH, and 4.5 g of tetrabutylammonium hydrogensulfate were added thereto. After the reaction mixture was stirred for 30 minutes at room temperature, 77 g of 2,6-difluorobenzyl chloride was slowly dropped thereto.
  • reaction mixture was stirred at a temperature of 60°C for 5 hours and cooled, and then, a separated organic layer was washed with water and then dried by using magnesium sulfate and concentrated, and the concentrate was separated by silicagel column chromatography to obtain 88 g of 5-((2,6-difluorobenzyloxy)methyl)-5-methyl-3-o-tolyl-4,5-dihydroisoxazole.
  • reaction mixture was stirred at room temperature overnight, and then, diluted with dichloromethane and then washed with water, and the obtained organic layer was dried by using magnesium sulfate and concentrated, and the concentrate was separated by silicagel column chromatography to obtain 400 mg of 3-(2-chlorophenyl)-5-((2,6-difluorobenzyloxy)methyl)-5-methyl-4,5-dihydroisoxazole.
  • reaction mixture was stirred at room temperature overnight, and then, diluted with dichloromethane, and then, washed with water, and the obtained organic layer was dried by using magnesium sulfate and concentrated, and the concentrate was separated by silicagel column chromatography to obtain 450 mg of 3-(2-bromophenyl)-5-((2,6-difluorobenzyloxy)methyl)-5-methyl-4,5-dihydroisoxazole.
  • reaction mixture was stirred at room temperature overnight, and then, diluted with dichloromethane, and then, washed with water, and the obtained organic layer was dried by using magnesium sulfate and concentrated, and the concentrate was separated by silicagel column chromatography to obtain 385 mg of 5-((2,6-difluorobenzyloxy)methyl)-3-(2-fluorophenyl)-5-methyl-4,5-dihydroisoxazole.
  • reaction mixture was stirred at room temperature overnight, and then, diluted with dichloromethane, and then, washed with water, and the obtained organic layer was dried by using magnesium sulfate and concentrated, and the concentrate was separated by silicagel column chromatography to obtain 410 mg of 5-((2,6-difluorobenzyloxy)methyl)-5-methyl-3-(2-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole.
  • a rectangular plastic pot having a surface area of 300 cm2 was filled with sandy loam soil and mixed bed soil which were mixed at a ratio of 1:1, and then, barnyardrass (Echinochloa crusgalli ), large crabgrass ( Digitaria sanguinalis ), blackgrass ( Alopecurus myosuroides), and annual bluegrass ( Poa annua ), which are grass weeds, were seeded thereto.
  • barnyardrass Echinochloa crusgalli
  • large crabgrass Digitaria sanguinalis
  • blackgrass Alopecurus myosuroides
  • Poa annua which are grass weeds
  • the spraying was performed by using a track sprayer (R&D Sprayer, USA) equipped with a Teejet 8002 (Spraying Systems Co., USA) nozzle, and a spraying amount was adjusted at 300 L/ha.
  • a spraying solution was prepared by dissolving test materials or references in acetone and adding the same amount of 0.2 %(v/v) tween 20 aqueous solution thereto.
  • Application rates were 500, 250, 125, and 62.5 g/ha.
  • the pots were placed in a greenhouse in which during day, the temperature was maintained at a temperature of 25 to 30°C, and during night, the temperature was maintained at a temperature of 15 to 25°C, and the pots were periodically irrigated.
  • Pots containing crops and weeds were prepared in the same manner as in Example 7, and then, in the second week in which crops and weeds entered into about 3 leaf stage, the test materials and the references were sprayed thereto in the same manner as described above.
  • the rates were 1,000, 500, 250, and 125 g/ha.
  • herbicidal efficacy and phytotoxicity to the respective weeds and crops were evaluated in a scale of 0 to 10 (0: no effects, 10: complete death). Results thereof are shown in Table 5.
  • Example 9 Structural activity relationships of the compounds of the present invention and the reference compounds
  • the compound represented by Formula 1 is equivalent to a compound represented by Formula 2a in which R1 is a phenyl substituted with alkyl, halogen, or haloalkyl at an ortho position, and R7 is a phenyl substituted with fluorines at 2,6-positions.
  • R1 indicates a C1 to C4 alkyl group, a halogen group, or a haloalkyl group
  • R2 indicates a hydrogen, a methyl group, or an ethyl group
  • R3 and R4 each indicates a fluorine.
  • the other compounds include a phenylisoxazoline derivative that is not substituted (substituted with a hydrogen); a phenylisoxazoline derivative that is substituted at other positions than 2(ortho)-position (controls H, F and G), or an isoxazoline derivative including a benzyl group that is not simultaneously substituted with fluorine at 2, 6-positions (control B, C, D and E). These materials have much lower activity than compounds of Formula 1.
  • R8 of Formula 2d is a hydrogen, haloalkyl, haloalkenyl, or a substituted aryl, it does not provide any information useful to predict structure-activity relation according to the kind or position of substituent in the phenyl ring.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
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  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (8)

  1. Ortho-substituierte, auf Phenylisoxazolin basierte Verbindung mit 2,6-Difluorbenzyloxymethyl, dargestellt durch Formel 1, oder ein Razemat oder Enantiomer davon:
    Figure imgb0037
     wobei R1 eine C1 bis C4 Alkylgruppe, eine Halogengruppe oder eine Haloalkylgruppe bezeichnet, R2 einen Wasserstoff, eine Methylgruppe oder eine Ethylgruppe bezeichnet, und R3 und R4 jeweils ein Fluor bezeichnen.
  2. Ortho-substituierte, auf Phenylisoxazolin basierende Verbindung oder das Razemat oder Enantiomer davon nach Anspruch 1, wobei R1 eine Methylgruppe, eine Fluorgruppe, eine Bromgruppe oder eine Trifluormethylgruppe ist, R2 einen Wasserstoff, eine Methylgruppe oder eine Ethylgruppe ist, und R3 und R4 jeweils eine Fluorgruppe ist.
  3. Ortho-substituierte, auf Phenylisoxazolin basierende Verbindung oder das Razemat oder Enantiomer davon nach Anspruch 1, wobei die Phenylisoxazolin basierende Verbindung oder das Razemat oder Enantiomer ausgewählt ist aus
    5-((2,6-Difluorbenzyloxy)methyl)-5-methyl-3-O-tolyl-4,5-dihydroisoxazol,
    3-(2-Chlorphenyl)-5-((2,6-difluorbenzyloxy)methyl)-5-methyl-4,5-dihydroisoxazol,
    3-(2-Bromphenyl)-5-((2,6-difluorbenzyloxy)methyl)-5-methyl-4,5-dihydroisoxazol,
    5-((2,6-Difluorbenzyloxy)methyl)-3-(2-fluorphenyl)-5-methyl-4,5-dihydroisoxazol) und
    5-((2,6-Difluorbenzyloxy)methyl)-5-methyl-3-(2-(trifluormethyl)phenyl)-4,5-dihydroisoxazol.
  4. Herbizid, als aktiven Wirkstoff die ortho-substituierte, auf Phenylisoxazolin basierende Verbindung umfassend oder das Razemat oder Enantiomer davon nach einem der Ansprüche 1-3.
  5. Herbizid nach Anspruch 4, wobei das Herbizid die ortho-substituierte, auf Phenylisoxazolin basierende Verbindung oder das Razemat oder Enantiomer davon als einen einzigen aktiven Wirkstoff in einer Menge von 0,5 bis 80 Gew.-% basierend auf einem Endprodukt umfasst.
  6. Herbizid nach Anspruch 4, wobei das Herbizid die ortho-substituierte, auf Phenylisoxazolin basierende Verbindung oder das Razemat oder Enantiomer davon als einen aktiven Wirkstoff eines gemischten Produkts in einer Menge von 0,5 bis 40 Gew.-% basierend auf einem Endprodukt umfasst.
  7. Verfahren zum selektiven Kontrollieren von Grasunkraut, umfassend die Behandlung mit der ortho-substituierten, auf Phenylisoxazolin basierenden Verbindung oder dem Razemat oder Enantiomer davon nach einem der Ansprüche 1-3, vor oder nach dem Auftreten des Grasunkrauts.
  8. Verfahren nach Anspruch 7, wobei das Grasunkraut Echinochloa crusgalli, Digitaria sanguinalis, Alopecurus mysuroides oder Poa annua ist.
EP12838839.4A 2011-10-04 2012-05-18 Phenylisoxazolinverbindung mit herbiziden eigenschaften und ihre verwendung Active EP2765129B1 (de)

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KR1020110100842A KR101093102B1 (ko) 2011-10-04 2011-10-04 제초활성을 가지는 페닐이속사졸린계 화합물 및 이의 용도
PCT/KR2012/003973 WO2013051776A1 (ko) 2011-10-04 2012-05-18 제초활성을 가지는 페닐이속사졸린계 화합물 및 이의 용도

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CN103874691B (zh) 2015-09-02
BR112014007758A2 (pt) 2017-04-25
JP2014534185A (ja) 2014-12-18
AU2012319413A1 (en) 2014-04-03
EP2765129A4 (de) 2015-03-25
US9439432B2 (en) 2016-09-13
AU2012319413B2 (en) 2015-07-23
WO2013051776A1 (ko) 2013-04-11
US20140256553A1 (en) 2014-09-11
CN103874691A (zh) 2014-06-18
EP2765129A1 (de) 2014-08-13
CA2850481A1 (en) 2013-04-11
CA2850481C (en) 2016-02-23
KR101093102B1 (ko) 2011-12-13

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